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Chemistry
Heterocyclic Building Blocks
Piperidines
methylpiperidine
3-(2-Methylpiperidin-1-yl)propan-1-amine
Chemistry
Heterocyclic Building Blocks
Organic Building Blocks
Piperidines
Amines Aliphatic Heterocycles
methylpiperidine
2-methylpiperidine

[ CAS No. 25560-00-3 ] {[proInfo.proName]}

,{[proInfo.pro_purity]}
Cat. No.: {[proInfo.prAm]}
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Product Details of [ 25560-00-3 ]

CAS No. :25560-00-3 MDL No. :MFCD00006517
Formula : C9H20N2 Boiling Point : -
Linear Structure Formula :- InChI Key :YYAYTNPNFKPFNG-UHFFFAOYSA-N
M.W : 156.27 Pubchem ID :520211
Synonyms :

Safety of [ 25560-00-3 ]

Signal Word:Danger Class:8
Precautionary Statements:P280-P305+P351+P338-P310 UN#:3267
Hazard Statements:H314 Packing Group:Ⅲ
GHS Pictogram:

Application In Synthesis of [ 25560-00-3 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 25560-00-3 ]

[ 25560-00-3 ] Synthesis Path-Downstream   1~89

  • 1
  • [ 25560-00-3 ]
  • [ 86-38-4 ]
  • (6-chloro-2-methoxy-acridin-9-yl)-[3-(2-methyl-piperidino)-propyl]-amine [ No CAS ]
YieldReaction ConditionsOperation in experiment
With phenol at 100℃;
Reference： [1]Corse et al. [Journal of the American Chemical Society, 1946, vol. 68, p. 1911]
  • 2
  • [ 25560-00-3 ]
  • [ 61516-73-2 ]
  • [ 88981-82-2 ]
YieldReaction ConditionsOperation in experiment
66% at 100℃; for 16h;
Reference： [1]Butler; Nordin; L'Italien; Zweisler; Poschel; Marriott [Journal of Medicinal Chemistry, 1984, vol. 27, # 5, p. 684 - 691]
  • 3
  • [ 25560-00-3 ]
  • [ 17402-78-7 ]
  • [ 128554-88-1 ]
YieldReaction ConditionsOperation in experiment
In N,N-dimethyl-formamide at 80℃; Yield given;
Reference： [1]Guerrera; Salerno; Siracusa; Ronsisvalle; Caruso; Leone; Felice [Il Farmaco, 1990, vol. 45, # 1, p. 29 - 38]
  • 4
  • [ 25560-00-3 ]
  • [ 138993-25-6 ]
  • [ 149338-20-5 ]
YieldReaction ConditionsOperation in experiment
90% In N,N-dimethyl-formamide Ambient temperature;
Reference： [1]Guerrera; Salerno; Sarva; Siracusa; Lamartina; Caruso; Cutuli [Il Farmaco, 1992, vol. 47, # 9, p. 1149 - 1160]
  • 5
  • [ 25560-00-3 ]
  • [ 63960-69-0 ]
  • [ 85723-84-8 ]
  • [ 85723-61-1 ]
YieldReaction ConditionsOperation in experiment
6% In dichloromethane for 17h; Heating;
In dichloromethane for 17h; Heating; Yields of byproduct given;
Reference： [1]Wise; Butler; DeWald; Lustgarten; Coughenour; Downs; Heffner; Pugsley [Journal of Medicinal Chemistry, 1986, vol. 29, # 9, p. 1628 - 1637]
[2]Wise; Butler; DeWald; Lustgarten; Coughenour; Downs; Heffner; Pugsley [Journal of Medicinal Chemistry, 1986, vol. 29, # 9, p. 1628 - 1637]
  • 6
  • [ 25560-00-3 ]
  • [ 56877-16-8 ]
  • [ 103068-95-7 ]
  • [ 103068-89-9 ]
YieldReaction ConditionsOperation in experiment
In dichloromethane for 17h; Heating;
Reference： [1]Wise; Butler; DeWald; Lustgarten; Coughenour; Downs; Heffner; Pugsley [Journal of Medicinal Chemistry, 1986, vol. 29, # 9, p. 1628 - 1637]
  • 7
  • [ 25560-00-3 ]
  • [ 7206-70-4 ]
  • 4-Amino-5-chloro-2-methoxy-N-[3-(2-methyl-piperidin-1-yl)-propyl]-benzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
With 1,1'-carbonyldiimidazole 1.) DMF, RT, 1 h, 2.) DMF, RT, overnight; Yield given. Multistep reaction;
Reference： [1]Orjales; Alonso-Cires; Labeaga; Innerarity; Corcostegui [European Journal of Medicinal Chemistry, 1995, vol. 30, # 7-8, p. 651 - 654]
  • 8
  • [ 25560-00-3 ]
  • [ 132715-34-5 ]
  • 3-[3-(2-Methyl-piperidin-1-yl)-propylamino]-1-propyl-1H-benzo[4,5]thieno[2,3-b]pyrazin-2-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
58%
Reference： [1]Guerrera; Salerno; Sarva; Siracusa; Rescifina; Scalia; Bianchi [European Journal of Medicinal Chemistry, 1996, vol. 31, # 7-8, p. 607 - 613]
  • 9
  • [ 25560-00-3 ]
  • [ 4428-22-2 ]
  • C23H28N2O3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
72% In 1,4-dioxane for 11h; Heating;
Reference： [1]Zawadowski, Teodor; Rajchman, Jolanta; Rump, Slawomir [Acta poloniae pharmaceutica, 1996, vol. 53, # 4, p. 283 - 286]
  • 10
  • [ 25560-00-3 ]
  • [ 5453-86-1 ]
  • [ 186641-16-7 ]
YieldReaction ConditionsOperation in experiment
80% In methanol reflux, 5 h, rt, 12 h;
Reference： [1]Nuhrich; Varache-Lembege; Vercauteren; Dokhan; Renard; Devaux [European Journal of Medicinal Chemistry, 1996, vol. 31, # 12, p. 957 - 964]
  • 11
  • [ 25560-00-3 ]
  • [ 5271-67-0 ]
  • [ 32024-15-0 ]
  • 3-[Dimethyl-(4-trimethylstannanyl-phenyl)-silanyl]-propionic acid [ No CAS ]
  • Thiophene-2-carboxylic acid (5,6-dimethoxy-biphenyl-3-ylmethyl)-[3-(2-methyl-piperidin-1-yl)-propyl]-amide [ No CAS ]
Reference： [1]Tetrahedron Letters,1998,vol. 39,p. 897 - 900
  • 12
  • [ 25560-00-3 ]
  • [ 15159-40-7 ]
  • [ 32024-15-0 ]
  • 3-[Dimethyl-(4-trimethylstannanyl-phenyl)-silanyl]-propionic acid [ No CAS ]
  • Morpholine-4-carboxylic acid (5,6-dimethoxy-biphenyl-3-ylmethyl)-[3-(2-methyl-piperidin-1-yl)-propyl]-amide [ No CAS ]
Reference： [1]Tetrahedron Letters,1998,vol. 39,p. 897 - 900
  • 13
  • [ 25560-00-3 ]
  • [ 32024-15-0 ]
  • [ 62348-13-4 ]
  • 3-[Dimethyl-(4-trimethylstannanyl-phenyl)-silanyl]-propionic acid [ No CAS ]
  • Isoxazole-5-carboxylic acid (5,6-dimethoxy-biphenyl-3-ylmethyl)-[3-(2-methyl-piperidin-1-yl)-propyl]-amide [ No CAS ]
Reference： [1]Tetrahedron Letters,1998,vol. 39,p. 897 - 900
  • 14
  • [ 25560-00-3 ]
  • [ 32024-15-0 ]
  • [ 137049-00-4 ]
  • 3-[Dimethyl-(4-trimethylstannanyl-phenyl)-silanyl]-propionic acid [ No CAS ]
  • 1-Methyl-1H-imidazole-4-sulfonic acid (5,6-dimethoxy-biphenyl-3-ylmethyl)-[3-(2-methyl-piperidin-1-yl)-propyl]-amide [ No CAS ]
Reference： [1]Tetrahedron Letters,1998,vol. 39,p. 897 - 900
  • 15
  • [ 25560-00-3 ]
  • [ 87199-16-4 ]
  • [ 62348-13-4 ]
  • 3-[(4-Bromo-phenyl)-dimethyl-silanyl]-propionic acid [ No CAS ]
  • Isoxazole-5-carboxylic acid biphenyl-3-ylmethyl-[3-(2-methyl-piperidin-1-yl)-propyl]-amide [ No CAS ]
Reference： [1]Tetrahedron Letters,1998,vol. 39,p. 897 - 900
  • 16
  • [ 25560-00-3 ]
  • [ 87199-17-5 ]
  • [ 62348-13-4 ]
  • 3-[(4-Bromo-phenyl)-dimethyl-silanyl]-propionic acid [ No CAS ]
  • Isoxazole-5-carboxylic acid biphenyl-4-ylmethyl-[3-(2-methyl-piperidin-1-yl)-propyl]-amide [ No CAS ]
Reference： [1]Tetrahedron Letters,1998,vol. 39,p. 897 - 900
  • 17
  • [ 25560-00-3 ]
  • [ 40138-16-7 ]
  • [ 62348-13-4 ]
  • 3-[(4-Bromo-phenyl)-dimethyl-silanyl]-propionic acid [ No CAS ]
  • Isoxazole-5-carboxylic acid biphenyl-2-ylmethyl-[3-(2-methyl-piperidin-1-yl)-propyl]-amide [ No CAS ]
Reference： [1]Tetrahedron Letters,1998,vol. 39,p. 897 - 900
  • 18
  • [ 25560-00-3 ]
  • [ 62348-13-4 ]
  • [ 127972-02-5 ]
  • 3-[(4-Bromo-phenyl)-dimethyl-silanyl]-propionic acid [ No CAS ]
  • Isoxazole-5-carboxylic acid (6-methoxy-biphenyl-3-ylmethyl)-[3-(2-methyl-piperidin-1-yl)-propyl]-amide [ No CAS ]
Reference： [1]Tetrahedron Letters,1998,vol. 39,p. 897 - 900
  • 19
  • [ 25560-00-3 ]
  • [ 32024-15-0 ]
  • [ 2493-02-9 ]
  • 3-[Dimethyl-(4-trimethylstannanyl-phenyl)-silanyl]-propionic acid [ No CAS ]
  • 3-(4-Bromo-phenyl)-1-(5,6-dimethoxy-biphenyl-3-ylmethyl)-1-[3-(2-methyl-piperidin-1-yl)-propyl]-urea [ No CAS ]
Reference： [1]Tetrahedron Letters,1998,vol. 39,p. 897 - 900
  • 20
  • [ 25560-00-3 ]
  • C69H67Cl2N9O20 [ No CAS ]
  • C78H85Cl2N11O19 [ No CAS ]
YieldReaction ConditionsOperation in experiment
90% With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate In dimethyl sulfoxide at 20℃; for 4h;
Reference： [1]Pavlov, Andrei Y.; Preobrazhenskaya, Maria N.; Malabarba, Adriano; Ciabatti, Romeo; Colombo, Luigi [Journal of Antibiotics, 1998, vol. 51, # 1, p. 73 - 81]
  • 21
  • [ 25560-00-3 ]
  • C73H74Cl2N8O20 [ No CAS ]
  • C82H92Cl2N10O19 [ No CAS ]
YieldReaction ConditionsOperation in experiment
85% With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate In dimethyl sulfoxide at 20℃; for 4h;
Reference： [1]Pavlov, Andrei Y.; Preobrazhenskaya, Maria N.; Malabarba, Adriano; Ciabatti, Romeo; Colombo, Luigi [Journal of Antibiotics, 1998, vol. 51, # 1, p. 73 - 81]
  • 22
  • [ 25560-00-3 ]
  • C74H76Cl2N8O20 [ No CAS ]
  • C83H94Cl2N10O19 [ No CAS ]
YieldReaction ConditionsOperation in experiment
87% With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate In dimethyl sulfoxide at 20℃; for 4h;
Reference： [1]Pavlov, Andrei Y.; Preobrazhenskaya, Maria N.; Malabarba, Adriano; Ciabatti, Romeo; Colombo, Luigi [Journal of Antibiotics, 1998, vol. 51, # 1, p. 73 - 81]
  • 23
  • [ 25560-00-3 ]
  • [ 79-08-3 ]
  • [ 261163-21-7 ]
  • [3-[3-(2-methyl-1-piperidinyl)propyl]-2,5-dioxo-1-imidazolidinyl]-carbamic acid 1,1-dimethylethyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
67% Multistep reaction;
Reference： [1]Wu, Shengde; Janusz, John M. [Tetrahedron Letters, 2000, vol. 41, # 8, p. 1165 - 1169]
YieldReaction ConditionsOperation in experiment
With methanol; ammonia; nickel at 100℃; Hydrogenation;
With ethanol; sodium
  • 25
  • [ 25560-00-3 ]
  • [ 26752-70-5 ]
  • 7-amino-6-(2,6-dichloro-phenyl)-2-[3-(2-methyl-piperidin-1-yl)-propylamino]-pyrido[2,3-d]pyrimidine [ No CAS ]
YieldReaction ConditionsOperation in experiment
60% With aminosulfonic acid at 160℃; for 24h;
Reference： [1]Schroeder; Hamby; Connolly; Grohar; Winters; Barvian; Moore; Boushelle; Crean; Kraker; Driscoll; Vincent; Elliott; Lu; Batley; Dahring; Major; Panek; Doherty; Hollis Showalter [Journal of Medicinal Chemistry, 2001, vol. 44, # 12, p. 1915 - 1926]
  • 26
  • [ 25560-00-3 ]
  • [ 1210-33-9 ]
  • N-[3-(2-methylpiperidin-1-yl)propyl]-10,11-dihydro-5H-dibenzo[a,d][7]annulen-5-amine [ No CAS ]
YieldReaction ConditionsOperation in experiment
87% With sodium carbonate; sodium iodide In dichloromethane for 1h; Heating;
Reference： [1]Duart, María J.; Antón-Fos, Gerardo M.; Alemán, Pedro A.; Gay-Roig, Joan B.; González-Rosende, María E.; Gálvez, Jorge; García-Domenech, Ramón [Journal of Medicinal Chemistry, 2005, vol. 48, # 4, p. 1260 - 1264]
  • 27
  • [ 25560-00-3 ]
  • [ 4752-10-7 ]
  • [3-(2-methyl-piperidin-1-yl)-propyl]-tetrazolo[5,1-<i>a</i>]phthalazin-6-yl-amine [ No CAS ]
YieldReaction ConditionsOperation in experiment
73% Multistep reaction;
Reference： [1]Hwang, Jong Yeon; Choi, Hyung-Sub; Gong, Young-Dae [Tetrahedron Letters, 2005, vol. 46, # 17, p. 3107 - 3110]
  • 28
  • [ 917603-21-5 ]
  • [ 25560-00-3 ]
  • 4-((2R,3R,4S,5R)-3,4-Dihydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-1-methyl-7-[3-(2-methyl-piperidin-1-yl)-propylamino]-1,4-dihydro-pyrazolo[4,3-d]pyrimidin-5-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
Stage #1: 1-methyl-4-β-D-ribofuranosyl-5-oxo-7-thiomethyl-pyrazolo[4,3-d]pyrimidine With 2,6-dimethylpyridine; polystyrene monomethoxytrityl chloride resin In N,N-dimethyl-formamide at 20℃; for 72h; Stage #2: 3-(2-Methyl-piperidino)-propylamin In 1-methyl-pyrrolidin-2-one at 80℃; for 24h; Stage #3: With 1,1,1,3',3',3'-hexafluoro-propanol In dichloromethane at 50℃; for 24h;
Reference： [1]Ramasamy, Kanda S.; Amador, Roberto B.; Habib, Qazi; Rong, Frank; Han, Xiaogang; Li, David Y.; Huang, Jingfan; Hong, Zhi; An, Haoyun [Nucleosides, nucleotides and nucleic acids, 2005, vol. 24, # 10-12, p. 1947 - 1970]
  • 29
  • [ 25560-00-3 ]
  • C15H8ClFN2O3 [ No CAS ]
  • 3-(2-fluorophenyl)-2,4-dioxo-1,2,3,4-tetrahydroquinazoline-7-carboxylic acid [3-(2-methyl-piperidin-1-yl)-propyl]amide [ No CAS ]
YieldReaction ConditionsOperation in experiment
In dichloromethane at 0 - 20℃; for 2h; 91 Example 91 : Synthesis of 3-(2-fluorophenyl)-2,4-dioxo-1 , 2,3,4- tetrahydroquinazoline-7-carboxylic acid [3-(2-methyl-piperidin-1 -yl)-propyl]-amide (Compound 91) 3-(2-Fluorophenyl)-2,4-dioxo-1 ,2,3,4-tetrahydroquinazoline-7-carboxylic acid (99 mg, 0.329 mmol) was dissolved in thionyl chloride (4 ml). The resultant was refluxed with stirring for 2 hours at 85°C, and then, production of acyl chloride was checked by TLC. The produced acyl chloride was concentrated under a reduced pressure, and the residue was maintained under vacuum for about 8 hours. The resulting material was dissolved in purified dichloromethane (4 ml), to which 3-(2-methyl-piperidin-1-yl)-propylamine (85 ml, 0.493 mmol) was slowly added dropwise at 0°C for a reaction, and the resultant was then stirred for two hours at room temperature. After the reaction was completed, the reaction solution was concentrated under a reduced pressure, and then the concentrated solution was filtered through silica gel (dicholoromethane:methanol:ammonia solution=200:10:1 ) to obtain 35mg of the desired compound (25%).1H NMR (400 MHz, DMSO-d6) δ 11.79 (s, 1H), 8.77 (bs, 1 H), 8.01 (d, J = 8.1 Hz, 1 H), 7.71 (s, 1 H), 7.60 (d, J = 8 Hz, 1 H), 7.52-7.48 (m, 2H), 7.41-7.31 (m, 2H), 3.28-3.26 (m, 2H), 2.79-2.66 (m, 2H), 2.27-2.24 (m, 2H), 2.05 (bs, 1 H), 1.67- 1.63 (m, 2H), 1.56-1.53 (m, 4H), 1.21-1.18 (m, 2H), 0.97 (d, J = 5.7 Hz, 3H)
Reference： [1]Current Patent Assignee: KOREA INSTITUTE OF SCIENCE AND TECHNOLOGY - WO2008/7835, 2008, A1 Location in patent: Page/Page column 72
  • 30
  • [ 25560-00-3 ]
  • C16H11ClN2O4 [ No CAS ]
  • 3-(2-methoxyphenyl)-2,4-dioxo-1,2,3,4-tetrahydroquinazoline-7-carboxylic acid [3-(2-methyl-piperidin-1-yl)-propyl]amide [ No CAS ]
YieldReaction ConditionsOperation in experiment
In dichloromethane at 0 - 20℃; for 2h; 94 Example 94: Synthesis of 3-(2-methoxyphenyl)-2,4-dioxo-1 ,2,3,4- tetrahydroquinazoline-7-carboxylic acid [3-(2-methyl-piperidin-1-yl)-propyl]-amide (Compound 94)3-(2-Methoxyphenyl)-2,4-dioxo-1 ,2,3,4-tetrahydroquinazoline-7-carboxylic acid (90 mg, 0.288 mmol) was dissolved in purified dichloromethane (3 ml), oxalyl chloride (1 ml) and a catalytic amount of dimethyl formamide. The resultant was then stirred for two hours at room temperature, and then, production of acyl chloride was checked by TLC. The produced acyl chloride was concentrated under a reduced pressure, and the residue was maintained under vacuum for about 8 hours. The resulting material was dissolved in purified dichloromethane (4 ml), to which 3-(2-methyl-piperidin-1-yl)-propylamine (89 ml, 0.518 mmol) was slowly added dropwise at 0°C for a reaction, and the resultant was then stirred for two hours at room temperature. After the reaction was completed, the reaction solution was concentrated under a reduced pressure, and the concentrated solution was filtered through silica gel (dicholoromethane:methanol:ammonia solution=200:10:1 ) to obtain 15 mg of the desired compound (12%).1H NMR (400 MHz, DMSO-d6) δ 11.70 (s, 1H), 8.75 (bs, 1H), 7.64 (s, 1 H), 7.59 (d, J = 8.2 Hz, 1 H), 7.42 (t, J = 7.5 Hz, 1 H), 7.27 (d, J = 7.4 Hz, 1 H), 7.16 (d, J = 8.2 Hz, 1 H), 7.03 (t, J = 7.2 Hz, 1 H), 3.71 (s, 3H), 3.28-3.26 (m, 2H), 2.79- 2.67 (m, 2H), 2.27 (bs, 2H), 2.07 (bs, 1 H), 1.68-1.64 (m, 2H), 1.56-1.39 (m, 4H), 1.22-1.19 (m, 2H), 0.98 (d, J = 5.9 Hz, 3H)
Reference： [1]Current Patent Assignee: KOREA INSTITUTE OF SCIENCE AND TECHNOLOGY - WO2008/7835, 2008, A1 Location in patent: Page/Page column 73-74
  • 31
  • [ 25560-00-3 ]
  • C16H10ClFN2O3 [ No CAS ]
  • 3-(2-fluorobenzyl)-2,4-dioxo-1,2,3,4-tetrahydroquinazoline-7-carboxylic acid [3-(2-methyl-piperidin-1-yl)-propyl]amide [ No CAS ]
YieldReaction ConditionsOperation in experiment
In dichloromethane at 0 - 20℃; for 2h; 97 Example 97: Synthesis of 3-(2-fluorobenzyl)-2,4-dioxo-1 ,2,3,4- tetrahydroquinazoline-7-carboxylic acid [3-(2-methyl-piperidin-1-yl)-propyl]-amide (Compound 97)3-(2-Fluorobenzyl)-2,4-dioxo-1 ,2,3,4-tetrahydroquinazoline-7-carboxylic acid (99.4 mg, 0.316 mmol) was dissolved in thionyl chloride (4 ml). The resultant was refluxed with stirring for 2 hours at 85°C, and then, production of acyl chloride was checked by TLC. The produced acyl chloride was concentrated under a reduced pressure, and the residue was maintained under vacuum for about 8 hours. The resulting material was dissolved in purified dichloromethane (4 ml), to which 3-(2-methyl-piperidin-1-yl)-propylamine (83 μl, 0.474 mmol) was slowly added dropwise at O0C for a reaction, and the resultant was then stirred for two hours at room temperature. After the reaction was completed, the reaction solution was concentrated under a reduced pressure, and then the concentrated solution was filtered through silica gel (dicholoromethane:methanol:ammonia solution=200:10:1 ) to obtain 68.8 mg of the desired compound (48%).1H NMR (300 MHz, DMSO-d6) δ 11.71 (s, 1H), 8.75 (s, 1 H), 8.00 (d, J = 8.2 Hz, 1 H), 7.62-7.57 (m, 2H), 7.28 (t, J = 7.1 Hz, 1 H), 7.21-7.07 (m, 3H), 5.13 (s, 2H), 3.28-3.26 (m, 2H), 2.81-2.72 (m, 2H), 2.31-2.08 (m, 1 H), 2.08-1.96 (m, 1 H), 1.96-1.93 (m, 1 H), 1.69-1.67 (m, 2H), 1.56-1.43 (m, 5H), 1.43-1.22 (m, 3H), 1.01- 0.99 (m, 3H)
Reference： [1]Current Patent Assignee: KOREA INSTITUTE OF SCIENCE AND TECHNOLOGY - WO2008/7835, 2008, A1 Location in patent: Page/Page column 75-76
  • 32
  • [ 25560-00-3 ]
  • C17H13ClN2O4 [ No CAS ]
  • 3-(2-methoxybenzyl)-2,4-dioxo-1,2,3,4-tetrahydroquinazoline-7-carboxylic acid [3-(2-methyl-piperidin-1-yl)-propyl]amide [ No CAS ]
YieldReaction ConditionsOperation in experiment
In dichloromethane at 0 - 20℃; for 2h; 100 Example 100: Synthesis of 3-(2-methoxybenzyl)-2,4-dioxo-1 ,2,3,4- tetrahydroquinazoline-7-carboxylic acid [3-(2-methyl-piperidin-1-yl)-propyl]-amide (Compound 100)3-(2-Methoxybenzyl)-2,4-dioxo-1 ,2,3,4-tetrahydroquinazoline-7-carboxylic acid (90 mg, 0.276 mmol) was dissolved in dichloromethane, to which oxalyl chloride (0.5 ml) and two drops of dimethyl formamide were added. The resultant was stirred at room temperature, and then, the production of acyl chloride was checked by TLC. The produced acyl chloride was concentrated under a reduced pressure, and the residue was maintained under vacuum for about 8 hours. The resulting material was dissolved in purified dichloromethane (4 ml), to which 3-(2- methyl-piperidin-1-yl-propylamine (71.8 μl, 0.414 mmol) was slowly added dropwise at O0C for a reaction, and the resultant was then stirred for two hours at room temperature. After the reaction was completed, the reaction solution was concentrated under a reduced pressure, and the concentrated solution was filtered through silica gel (dicholoromethane:methanol:ammonia solution=200:10:1 ) to obtain 34 mg of the desired compound (26%).1H NMR (300 MHz, DMSO-d6) δ 11.68 (s, 1H), 8.74 (s, 1 H), 8.00 (d, J = 8.1 Hz, 1 H), 7.59 (t, J = 10.7 Hz, 2H), 7.19 (t, J = 6.0 Hz, 1 H), 7.01 (d, J = 8.2 Hz 1 H), 6.82-6.79 (m, 2H), 5.04 (s, 2H), 3.84 (s, 3H), 3.32-3.22 (m, 2H), 2.93-2.61 (m, 2H), 2.27-2.21 (m, 2H), 2.13-1.89 (m, 1 H), 1.67-1.50 (m, 6H), 1.20-1.18 (m, 2H), 0.97 (d, J = 6.2 Hz, 3H)
Reference： [1]Current Patent Assignee: KOREA INSTITUTE OF SCIENCE AND TECHNOLOGY - WO2008/7835, 2008, A1 Location in patent: Page/Page column 76-77
  • 33
  • [ 25560-00-3 ]
  • C15H15ClN2O3 [ No CAS ]
  • 3-cyclohexyl-2,4-dioxo-1,2,3,4-tetrahydroquinazoline-7-carboxylic acid [3-(2-methyl-piperidin-1-yl)-propyl]amide [ No CAS ]
YieldReaction ConditionsOperation in experiment
In dichloromethane at 0 - 20℃; for 2h; 103 Example 103: Synthesis of 3-cyclohexyl-2,4-dioxo-1 ,2,3,4- tetrahydroquinazoline-7-carboxylic acid [3-(2-methyl-piperidin-1 -yl)-propyl]-amide (Compound 103)3-Cyclohexyl-2,4-dioxo-1 ,2,3,4-tetrahydroquinazoline-7-carboxylic acid (90 mg, 0.312 mmol) was dissolved in thionyl chloride (4 ml). The resultant was refluxed with stirring for 2 hours at 850C, and then, production of acyl chloride was checked by TLC. The produced acyl chloride was concentrated under a reduced pressure, and the residue was maintained under vacuum for about 8 hours. The resulting material was dissolved in purified dichloromethane (4 ml), to which 3-(2- methyl-piperidin-1-yl)-propylamine (65 ml, 0.374 mmol) was slowly added dropwise at 00C for a reaction, and the resultant was then stirred for two hours at room temperature. After the reaction was completed, the reaction solution was concentrated under a reduced pressure, and then the concentrated solution was filtered through silica gel (dicholoromethane:methanol:ammonia solution=200:10:1 ) to obtain 64 mg of the desired compound (48%). 1H NMR (300 MHz, DMSO-Cl6) δ 11.43 (s, 1 H), 8.69 (bs, 1 H), 7.96 (d, J =8.7 Hz, 1 H), 7.55-7.52 (m, 2H), 4.76-4.68 (m, 1 H), 3.26-3.22 (m, 2H), 2.79-2.64 (m,2H), 2.39-2.35 (m, 2H), 2.27-2.20 (m, 2H), 2.10-2.00 (m, 1 H), 1.82-1.78 (m, 2H),1.67-1.51 (m, 8H), 1.41-1.18 (m, 6H), 0.97 (d, J = 6.2 Hz, 3H)
Reference： [1]Current Patent Assignee: KOREA INSTITUTE OF SCIENCE AND TECHNOLOGY - WO2008/7835, 2008, A1 Location in patent: Page/Page column 78-79
  • 34
  • [ 25560-00-3 ]
  • [ 953077-72-0 ]
  • C27H30N4O4S [ No CAS ]
YieldReaction ConditionsOperation in experiment
In tetrahydrofuran; tetrachloromethane at 0 - 40℃; for 1.5h; 25 Production Examples 15 to 28; Fourteen compounds shown in Table 2 were obtained by the same procedures as in Production Example 14, except that amines shown in Table 2 were used in place of diethylamine. The product was identified by 1H-NMR and MALDI-TOFMS. In Table 2, Me denotes methyl group, Et denotes ethyl group, Pr denotes normal propyl group, i-Pr denotes 2-propyl group and Bu denotes butyl group. Production Example 14: Synthesis of Compound (36); A THF (8 mL) solution of 3.0g of diethylamine was added dropwise to a carbon tetrachloride solution of Compound (1) prepared from 5.8g of Compound (I) according to Production Example 1, over 30 minutes under cooling with ice. After heating the reaction mixture at 40°C, the mixture was stirred for 1 hour followed by re-precipitation to give 2.0g of Compound (36). The product was identified by 1H-NMR, TOFMS and elementary analysis. 1H-NMR (270 MHz, CDCl3): δ 1.01 (6H, t, J = 7.0 Hz, CH3), 3.31 (4H, q, J = 7.0 Hz, CH3CH2), 4.58 (2H, br-s, NH2), 7.48-7.72 (8H, m, Ar-H), 8.05 (1H, br-s, NH). TOFMS; Calculated: 423.13; Found: 423.62. Elemental Analysis (C22H21N3O4S); Calculated: C, 62.40; H, 5.00; N, 9.92; Found: C, 62.31; H, 5.12; N, 9.88.
Reference： [1]Current Patent Assignee: TOYO INK SC HOLDINGS COMPANY, LIMITED - EP1892240, 2008, A1 Location in patent: Page/Page column 34
  • 35
  • [ 25560-00-3 ]
  • [ 681243-44-7 ]
  • 3-ethyl-2-methoxy-6-([2-({3-[(2R)-2-methyl-1-piperidinyl]propyl}amino)phenyl]sulfonyl}amino)benzoic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
50% With triethylamine In acetonitrile at 90℃; for 72h;
With triethylamine In acetonitrile at 150℃; for 0.916667h; Microwave; 319 EXAMPLE 319 3-Ethyl-2-methoxy-6-([2-({3-[(2R)-2-methyl-1-piperidinyl]propyl}amino)phenyl]sulfonyl}amino)benzoic acid EXAMPLE 319 3-ethyl-2-methoxy-6-([2-({3-[(2R)-2-methyl-1-piperidinyl]propyl}amino)phenyl]sulfonyl}amino)benzoic acid [0605] A mixture of Example 318E (50 mg, 0.14 mmol), triethylamine (0.1 mL, 0.71 mmol), acetonitrile (1 mL) and 1-(3-aminopropyl)-2-pipecoline (177 mg, 1.1 mmol) was purged with argon, sealed in a vial and microwaved at 150° C. for 55 minutes. Purification by preparative HPLC on a Waters Symmetry C8 column (25 mm×100 mm, 7 μm particle size) using a gradient of 10% to 100% acetonitrile/0.1% aqueous TFA over 8 minutes (10 minute run time) at a flow rate of 40 mL/min provided the desired product. MS (ESI(+)) m/e 490 (M+H)+; (ESI(-)) m/e 488 (M-H)-; 1H NMR (300 MHz, DMSO-d6) δ 13.24 (br s, 1H), 9.71 (br s, 1H), 7.58 (dd, 1H), 7.42 (t, 1H), 7.13 (d, 1H), 6.87 (dd, 1H), 6.67 (m, 2H), 6.05 (m, 1H), 3.69 (s, 3H), 3.36 (m, 2H), 3.12 (m, 2H), 3.05 (m, 2H), 2.88 (m, 1H), 2.54 (q, 2H), 1.86 (m, 4H), 1.64 (m, 2H), 1.43 (m, 2H), 1.20 (d, 3H), 1.10 (t, 3H).
Reference： [1]Wang, Gary T.; Mantei, Robert A.; Kawai, Megumi; Tedrow, Jason S.; Barnes, David M.; Wang, Jieyi; Zhang, Qian; Lou, Pingping; Garcia, Lora A.; Bouska, Jennifer; Yates, Melinda; Park, Chang; Judge, Russell A.; Lesniewski, Richard; Sheppard, George S.; Bell, Randy L. [Bioorganic and Medicinal Chemistry Letters, 2007, vol. 17, # 10, p. 2817 - 2822]
[2]Current Patent Assignee: ABBVIE INC - US2004/167128, 2004, A1 Location in patent: Page 65
  • 36
  • [ 25560-00-3 ]
  • [ 623581-58-8 ]
  • C30H39N5O4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Stage #1: C21H21N3O5 With dicyclohexyl-carbodiimide; Kaiser oxime resin In dichloromethane for 18h; Stage #2: 3-(2-Methyl-piperidino)-propylamin In dichloromethane for 18h; Further stages.;
Reference： [1]Wei, Robert G.; Adler, Marc; Davey, David; Ho, Elena; Mohan, Raju; Polokoff, Mark; Tseng, Jih-Lie; Whitlow, Marc; Xu, Wei; Yuan, Shendong; Phillips, Gary [Bioorganic and Medicinal Chemistry Letters, 2007, vol. 17, # 9, p. 2499 - 2504]
  • 37
  • [ 25560-00-3 ]
  • 1-tert-Butyl-3-{6-(2,6-dichloro-phenyl)-2-[3-(2-methyl-piperidin-1-yl)-propylamino]-pyrido[2,3-d]pyrimidin-7-yl}-urea [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: 60 percent / sulfamic acid / 24 h / 160 °C 2.1: NaH / dimethylformamide / 1 h / 20 °C 2.2: 31 percent / dimethylformamide / 18 h / 20 °C
Reference： [1]Schroeder; Hamby; Connolly; Grohar; Winters; Barvian; Moore; Boushelle; Crean; Kraker; Driscoll; Vincent; Elliott; Lu; Batley; Dahring; Major; Panek; Doherty; Hollis Showalter [Journal of Medicinal Chemistry, 2001, vol. 44, # 12, p. 1915 - 1926]
  • 38
  • [ 25560-00-3 ]
  • [ 128554-99-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: dimethylformamide / 80 °C 2: 70 percent / H2 / 5percent Pd/C / acetic acid / 6 h / Ambient temperature
Reference： [1]Guerrera; Salerno; Siracusa; Ronsisvalle; Caruso; Leone; Felice [Il Farmaco, 1990, vol. 45, # 1, p. 29 - 38]
  • 39
  • [ 25560-00-3 ]
  • [ 305356-24-5 ]
  • C31H34Cl2N4O3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide
Reference： [1]Current Patent Assignee: MERCK & CO INC - US6348482, 2002, B1 Location in patent: Page column 47-48
  • 40
  • [ 25560-00-3 ]
  • C17H15O3Pol [ No CAS ]
  • C26H35N2O3Pol [ No CAS ]
YieldReaction ConditionsOperation in experiment
4.1 EXAMPLE 4 Compounds FK to KV Step 1. Resin A from Step 1 Example 2 was suspended in dimethylformamide (30 ml) and then treated with phenethylamine (10 eqivalents). After standing at room temperature overnight the mixture was filtered to give resin G which was washed with (i) dimethylformamide, (ii) tetrahydrofuran, (iii) dichloromethane and then dried in a desiccator under high vacuum for 2 hours. By proceeding in a similar manner but replacing phenethylamine by allylamine, isobutylamine, (cyclohexyl)methylamine, 3-(2-oxo-1-pyrrolydinyl)prop-1-ylamine, 4-phenyl-1-butylamine, piperonylamine, 3-(1-imidazolyl)prop-1-ylamine, 3-(2-methyl-1-piperdinyl)prop-1-ylamine, 2-(2-pyridinyl)ethylamine, (2-acetamido)ethylamine or 2-methoxybenzylamine there were prepared resins H to R.
Reference： [1]Current Patent Assignee: SANOFI - US6352977, 2002, B1 Location in patent: Page column 63-64
  • 41
  • [ 705979-26-6 ]
  • [ 25560-00-3 ]
  • [ 705977-44-2 ]
YieldReaction ConditionsOperation in experiment
37% With triethylamine In o-xylene at 20 - 145℃; for 4h; Method for monosubstituted acylguanidine formation (General Method C): To a solution of 1- {2- [2- (5-BROMO-2-METHOXYPHENYL)- ETHYL]-3-FLUOROBENZOYL}-2-METHYLISOTHIOUREA (0.16 g, 0.38 mmol, 1 equiv) in o-xylene (1.7 mL) were added triethylamine (0.052 mL, 0.38 mmol, 1 equiv) and 1- (3-AMINOPROPYL)-2- pipecoline (0.067 mL, 0.38 mmol, 1 equiv). The solution was allowed to stir at 145 °C for 4 hours and then cooled to room temperature. Hexanes (2 mL) and dichloromethane (2 mL) were added and the solution concentrated to a volume of about 0.5 mL. The residue was purified by column chromatography (SI02) to give the desired acylguanidine, which was characterized as its bisformate salt (0.089 g, 0.053 mmol, 37%).
Reference： [1]Current Patent Assignee: ORE PHARMACEUTICALS - WO2004/50610, 2004, A2 Location in patent: Page 61-62
  • 42
  • [ 25560-00-3 ]
  • (3-(2-amino-6-chloropyrimidin-4-yl)-4-(benzyloxy)phenyl)(2-fluoro-4-methylphenyl)methanone [ No CAS ]
  • [3-(2-amino-6-[3-(2-methyl-1-piperidinyl)propyl]amino}-4-pyrimidinyl)-4-(benzyloxy)phenyl](2-fluoro-4-methylphenyl)methanone [ No CAS ]
YieldReaction ConditionsOperation in experiment
61% In 1,4-dioxane for 8h; 27 PREPARATION 27: Preparation of [3-(2-amino-6-[3-(2-methyl-1-piperidinyl)propyl]amino}-4-pyrimidinyl)-4-(benzyloxy)phenyl](2-fluoro-4-methylphenyl)methanone 36 mg (0.080 mmol) of the compound as obtained in PREPARATION 26 was dissolved in 2 ml of dioxane, and 0.28 ml (1.60 mmol) of 1- (3-AMINOPROPYL)-2- pipecoline was added thereto, followed by heating with stirring for 8 hours. When the reaction was completed, a product was extracted with ethyl acetate and washed two times with water. An organic layer was concentrated and then purified by column chromatography to give 28 mg of the title compound at 61% yield. 1H NMR (CDC13, ppm) ; 8 8.28 (1H, d), 7. 84 (1H, dt), 7.36 (7H, m), 7.38 (5H, m), 7.051 (2H, m), 6.95 (1H, d), 6.30 (1H, s), 5.21 (2H, s), 4.78 (2H, s), 3.29 (1H, M), 2.81 (2H, m), 2.41 (3H, s), 2.25 (2H, m), 2.09 (2H, m). 1.64 (6H. m), 1.31 (2H, m), 1.08 (3H, d). FAB MS (m/e) =568 [M++1]
Reference： [1]Current Patent Assignee: LG CHEM CO.,LTD. - WO2004/80979, 2004, A1 Location in patent: Page 63, 64
  • 43
  • [ 25560-00-3 ]
  • [ 66-99-9 ]
  • [ 862494-55-1 ]
YieldReaction ConditionsOperation in experiment
Stage #1: 3-(2-Methyl-piperidino)-propylamin; β-naphthaldehyde In dichloromethane at 20℃; Molecular sieve; Stage #2: With sodium tetrahydroborate In methanol for 0.5h; 24.1 2-Naphtaldehyde 1 g (6.4 mmol), 3-(2-methyl-piperidin-1-yl)-propylamine 0.99 g (6.4 mmol), in 25 mL of dry dichloromethane was added 5 g of molecular sieve. The reaction was stirred overnight at room temperature. The molecular sieve was filtered and dichloromethane was concentrated under vacuum. To the mixture was added 15 mL of dry methanol and sodium borohydride 0.3 g (8 mmol) after 30 minutes reaction goes to completion, methanol was concentrated under vacuum, and was diluted with chloroform, organic layer was washed with 2 times 20 mL water, followed with brine. The organic layer was dried over magnesium sulfate and concentrated under vacuum. The compound was purified using silica gel chromatography elution, with 3.5% methanol in chloroform, yield 0.6 g oil.
Stage #1: 3-(2-Methyl-piperidino)-propylamin; β-naphthaldehyde With molecular sieve In dichloromethane at 20℃; Stage #2: In methanol for 0.5h; 18.1 Step 1: Step 1: [3-(2-Methyl-piperidin-1-yl)-propyl]-naphthalen-2-ylmethyl-amine 2-Naphtaldehyde 1 g (6.4 mmol), 3-(2-methyl-piperidin-1-yl)-propylamine 0.99 g (6.4 mmol), in 25 mL of dry dichloromethane was added 5 g of molecular sieve. The reaction was stirred overnight at room temperature. The molecular sieve was filtered and dichloromethane was concentrated under vacuum. To the mixture was added 15 mL of dry methanol and sodium borohydride 0.3 g (8 mmol) after 30 minutes reaction goes to completion, methanol was concentrated under vacuum, and was diluted with chloroform, organic layer was washed with 2 times 20 mL water, followed with brine. The organic layer was dried over magnesium sulfate and concentrated under vacuum. The compound was purified using silica gel chromatography elution, with 3.5% methanol in chloroform, yield 0.6 g oil.
Reference： [1]Current Patent Assignee: CHEMOCENTRYX INC - US2005/214287, 2005, A1 Location in patent: Page/Page column 46
[2]Current Patent Assignee: CHEMOCENTRYX INC - US2006/74071, 2006, A1 Location in patent: Page/Page column 22
  • 44
  • [ 25560-00-3 ]
  • [ 580-13-2 ]
  • [ 862494-57-3 ]
YieldReaction ConditionsOperation in experiment
With potassium phosphate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl In 1,2-dimethoxyethane for 17h; Heating / reflux; 26.1 In round bottom flask under nitrogen, was added palladium (II) acetate 0.09 g (0.4 mmol), rac-2,2'-bis(diphenylphosphino)-1,1'-binaphtyl 0.53 g (0.8 mmol), tripotassium phospate mono basic 0.06 g (29 mmol), in 25 mL DME, to this mixture was added 2-bromonaphthalene 1.7 g (8.2 mmol), and 2-methyl-piperidine-N-propylamine 4 g (25.6 mmol). The mixture was refluxed 17 hours. The reaction mixture was filtered through celite and concentrated. The compound was purified using silica gel chromatography, elution with 5% methanol in chloroform. Yield to 0.47 g of compound
With dipotassium hydrogenphosphate In 1,2-dimethoxyethane for 17h; Heating / reflux; 20.1 Step 1: Step 1: [3-(2-Methyl-piperidin-1-yl)-propyl]-naphthalen-2-yl amine In round bottom flask under nitrogen, was added palladium (II) acetate 0.09 g (0.4 mmol), rac-2,2'-bis(diphenylphosphino)-1,1'-binaphtyl 0.53 g (0.8 mmol), tripotassium phospate mono basic 0.06 g (29 mmol), in 25 mL DME, to this mixture was added 2-bromonaphthalene 1.7 g (8.2 mmol), and 2-methyl-piperidine-N-propylamine 4 g (25.6 mmol). The mixture was refluxed 17 hours. The reaction mixture was filtered through celite and concentrated. The compound was purified using silica gel chromatography, elution with 5% methanol in chloroform. Yield to 0.47 g of compound.
Reference： [1]Current Patent Assignee: CHEMOCENTRYX INC - US2005/214287, 2005, A1 Location in patent: Page/Page column 48
[2]Current Patent Assignee: CHEMOCENTRYX INC - US2006/74071, 2006, A1 Location in patent: Page/Page column 23-24
  • 45
  • [ 25560-00-3 ]
  • [ 862494-59-5 ]
  • [ 862494-56-2 ]
YieldReaction ConditionsOperation in experiment
In dichloromethane at 20℃; 19.1 Step 1: Step 1: [3-(2-Methyl-piperidin-1-yl)-propyl]-(5-phenyl-thiazol-2ylmethyl)-amine Experimental condition analogous to Example 18, from 5-phenyl-thiazole-2-carbaldehyde 0.16 g (1.05 mmol), 3-(2-methyl-piperidin-1-yl)-propylamine 0.2 g (1.05 mmol), in 5 mL of dry dichloromethane was added 2 g of molecular sieve. The reaction was stirred overnight at room temperature. The molecular sieve was filtered and dichloromethane was concentrated under vaccum. To the mixture was added 15 mL of dry methanol and sodium borohydride 0.04 g (1.155 mmol) was added at 0° C. after 30 minutes reaction goes to completion. The reaction was quenched with 2 mL acetone, methanol was concentrated under vacuum, and was diluted with chloroform, organic layer was washed with 2 times 20 mL water, followed with brine. The organic layer was dried over magnesium sulfate and concentrated under vaccum. Yield 0.3 g of compound.
Reference： [1]Current Patent Assignee: CHEMOCENTRYX INC - US2006/74071, 2006, A1 Location in patent: Page/Page column 23
  • 46
  • [ 25560-00-3 ]
  • [ 112-67-4 ]
  • [ 151190-49-7 ]
YieldReaction ConditionsOperation in experiment
83% In dichloromethane 2 2-Methyl-l-[3-(N-hexadecanoyl)aminopropyl]piperidine (11) EXAMPLE 2 2-Methyl-l-[3-(N-hexadecanoyl)aminopropyl]piperidine (11) To a solution of 1-(3-aminopropyl)-2-pipecoline (1.00 g, 6.40 mmole) in methylene chloride (25 mL) was added palmitoyl chloride (1.73 g, 6.40 mmole) in small portions. The reaction mixture was stirred at room temperature overnight. The reaction mixture was washed twice with saturated aqueous sodium bicarbonate and once with brine. The organic layer was dried over magnesium sulfate and the salts removed by filtration. The solvent was removed under reduced pressure and the residue dried in vacuo to give the title compound (2.12 g, 83%), mp. 48°-50° C. 1 H NMR (300 MHz, CDCl3): δ0.883 (3H, t, J=6.5 Hz), 1.136 (3H, d, J=5.5 Hz), 1.254 (24H, bs), 1.60 to 1.70 (4H, m), 2.157 (2H, t, J=7.6 Hz), 2.37 to 2.39 (2H, m), 2.89 to 2.94 (3H, m), 3.24 to 3.27 (1H, m), 3.40 to 3.44 (1H, m), and 7.266 (1H, bs). Analysis calculated for C25 H50 N2 O.1/4H2 O C, 75.16; H, 12.61; N, 7.01. Found: C, 75.16; H, 12.69; N, 7.16.
Reference： [1]Current Patent Assignee: DUKE UNIVERSITY; SPHINX PHARMACEUTICALS CORPORATION - US5270310, 1993, A
  • 47
  • [ 25560-00-3 ]
  • [ 909782-30-5 ]
  • C50H56N10O3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
82% In 1,4-dioxane; acetone at 60 - 95℃; for 5h; 5 The thus-obtainedIntermediate G(acetone-containing cake) represented by the formula (26) was step by step added to a mixed solution of 320 g of 1,4-dioxane and 125 g of N-aminopropyl-2-pipecoline at a temperature of 60 °C or less. Then, the mixture was stirred at 95 °C for 5 hours. The reaction mixture was cooled to room temperature and then poured to 5 liters of water, to generate a precipitate. The precipitate was filtered, washed with water and dried to obtain 111 g (82%) of Pigment dispersing agent C represented by the formula (27) .
Reference： [1]Current Patent Assignee: TOYO INK SC HOLDINGS COMPANY, LIMITED - EP1702960, 2006, A2 Location in patent: Page/Page column 21
  • 48
  • [ 25560-00-3 ]
  • [ 95789-89-2 ]
  • 3-(1,6-dihydro-6-oxo-9H-purin-9-yl)-N-[3-(2-methylpipiridin-1-yl)propyl]propanamide [ No CAS ]
  • [ 138117-58-5 ]
YieldReaction ConditionsOperation in experiment
In acetonitrile 10 Synthesis of 3-(1,6-dihydro-6-oxo-9H-purin-9-yl)-N-[3-(2-methylpiperidin-1-yl)propyl]propanamide (AIT-0044) EXAMPLE 10 Synthesis of 3-(1,6-dihydro-6-oxo-9H-purin-9-yl)-N-[3-(2-methylpiperidin-1-yl)propyl]propanamide (AIT-0044) 0.565 g (3.62 mmol) of 1-(3-aminopropyl)-2-pipecoline was placed into a 10 ml round bottom flask with a magnetic stirring bar. The flask was heated to 120° C. and 250 mg (1.06 mmol) of 3-(1,6-dihydro-6-oxo-9H-purin-9-yl)propionic acid, ethyl ester (AIT-0027) was added. The mixture was heated for two hours at 120° C. and was allowed to cool. The resultant light orange viscous oil was treated with 8 ml acetonitrile and was stirred for about 25 min. The solution was filtered and the solid was washed with acetonitrile and then with ether. This yielded 254 mg of 3-(1,6-dihydro-6-oxo-9H-purin-9-yl)-N-[3-(2-methylpipiridin-1-yl)propyl]propanamide (AIT-0044) as an off-white solid.
Reference： [1]Current Patent Assignee: SPECTRUM PHARMACEUTICALS INC - US5091432, 1992, A
  • 49
  • [ 25560-00-3 ]
  • [ 350-46-9 ]
  • N1-[3-(2-methylpiperidin-1-yl)propyl]-4-nitro-1-aminobenzene [ No CAS ]
YieldReaction ConditionsOperation in experiment
With triethylamine In 1-methyl-pyrrolidin-2-one at 60℃; for 8h; 7.1 2 g of para-fluoronitrobenzene were added to a solution of 20 ml of N-methyl-pyrrolidinone, 1.65 g of 1-(3-aminopropyl)-2-pipecoline and 1.72 g of triethylamine. The reaction medium was heated at 60° C. for 8 hours and, after cooling to room temperature, was then poured into a water and ice mixture. The yellow precipitate formed was filtered off, reslurried in water and then dried over P2O5. 2.2 g of N-[3-(2-methyl-piperidin-1-yl)propyl]-4-nitro-1-aminobenzene (17) were obtained.
Reference： [1]Current Patent Assignee: L&apos;OREAL SA - US2006/26772, 2006, A1 Location in patent: Page/Page column 11
  • 50
  • [ 25560-00-3 ]
  • [ 1493-27-2 ]
  • [ 1023699-50-4 ]
YieldReaction ConditionsOperation in experiment
With potassium carbonate In N,N-dimethyl-formamide at 90℃; for 24h;
Reference： [1]Micco, Iolanda; Nencini, Arianna; Quinn, Joanna; Bothmann, Hendrick; Ghiron, Chiara; Padova, Alessandro; Papini, Silvia [Bioorganic and Medicinal Chemistry, 2008, vol. 16, # 5, p. 2313 - 2328]
  • 51
  • [ 25560-00-3 ]
  • [ 6046-93-1 ]
  • [ 1761-61-1 ]
  • [ 151802-42-5 ]
YieldReaction ConditionsOperation in experiment
22% In ethanol addn. of the aldehyde in abs. EtOH to the pyridine-compd. in EtOH at room temp., heating at ca 50°C for 4 h, addn. of the Cu-compd. over a period of 0.5 h with const. stirring; filtn., evapn. of the filtrate at room temp. for ca 3 d, collection of crystals by filtn., washing with EtOH/ligroin and drying under vac., no recrystn. from org. solvents without alteration of the compd.; elem. anal.;
Reference： [1]Chiari; Piovesana; Tarantelli; Zanazzi [Inorganic Chemistry, 1993, vol. 32, # 22, p. 4834 - 4838]
  • 52
  • [ 7154-73-6 ]
  • [ 27578-60-5 ]
  • [ 140-31-8 ]
  • [ 2038-03-1 ]
  • [ 25560-00-3 ]
  • [ 123-00-2 ]
  • [ 5036-48-6 ]
  • [ 7663-77-6 ]
  • [ 34035-03-5 ]
  • [ 1761-71-3 ]
  • [ 6864-37-5 ]
  • [ 2213-43-6 ]
  • [ 63234-71-9 ]
  • [ 5906-35-4 ]
  • [ 59983-39-0 ]
  • [ 1664-40-0 ]
  • [ 6530-09-2 ]
  • [ 108-00-9 ]
  • [ 109-55-7 ]
  • [ 51387-90-7 ]
  • [ 102-83-0 ]
  • [ 849908-66-3 ]
  • C15H17ClN2O [ No CAS ]
  • [ 849908-70-9 ]
  • [ 940358-24-7 ]
  • C16H19ClN2O [ No CAS ]
  • C19H19ClN2O [ No CAS ]
  • [ 849908-71-0 ]
  • C17H21ClN2O2 [ No CAS ]
  • [ 849908-67-4 ]
  • C17H21ClN2O [ No CAS ]
  • [ 880815-24-7 ]
  • C17H22ClN3O [ No CAS ]
  • C18H21ClN2O [ No CAS ]
  • [ 849908-65-2 ]
  • [ 932172-19-5 ]
  • [ 875001-79-9 ]
  • [ 849908-68-5 ]
  • [ 849908-69-6 ]
  • [ 849908-81-2 ]
  • [ 849908-75-4 ]
YieldReaction ConditionsOperation in experiment
With polymer-bound trimethyl ammonium cyanoborohydride; acetic acid; In 1,2-dichloro-ethane; at 20℃; for 24 - 36h;Combinatorial reaction / High throughput screening (HTS); All sixty diamines were separated in four groups based on their steric and electronic characteristics, Figures 1-4. Each diamine was measured in the amount of 0.05 g (approximately 0.3 mmol) and pooled together with the others in the group. Obtained diamine mixtures were dissolved in 5 ml of 1,2-dichloroethane and used for the syntheses. Each well of the 96-well filterplates was loaded with 0.2 ml of 1: 10 mixture of acetic acid: DCE, 0.03 ml of the diamine mixture in DCE (group 1, group 2, group 3, or group 4) to assure 0.04 mmol of the diamines per well, and shaken for 5 min at room temperature. Appropriate carbonyl compounds from the master plate (0.1 ml of 1.2 M solution) were added into corresponding wells of the reaction plates followed by the addition of (polystyrylmethyl) trimethylammonium cyanoborohydride, (0.020 g, 0.08 mmol per well). The reaction plates were sealed and placed on a shaker. The reaction was allowed to proceed 24-36 hours at room temperature. At the end, the reaction mixtures were filtered using a filtration manifold, and products were collected into four (one per group) collection plates. Solvents were evaporated in SpeedVac and formed residues were analyzed by mass spectrometry prior to biological screening. Mono and double alkylated products were observed in 1: 0.5 to 1: 2 ratios by mass spectral analysis.
Reference： [1]Patent: WO2005/34857,2005,A2 .Location in patent: Page/Page column 15; 22
  • 53
  • [ 25560-00-3 ]
  • [ 917889-50-0 ]
  • 3-(4-chloro-benzyl)-2,4-dioxo-1,2,3,4-tetrahydro-quinazoline-7-carboxylic acid [3-(2-methyl-piperidine-1-yl)-propyl]-amide [ No CAS ]
YieldReaction ConditionsOperation in experiment
17 3-(4-Chloro-benzyl)-2,4-dioxo-1,2,3,4-tetrahydro-quinazoline-7-carboxylic acid [3-(2-methyl-piperidine-1-yl)-propyl]-amide (Compound 17) Example 17 3-(4-Chloro-benzyl)-2,4-dioxo-1,2,3,4-tetrahydro-quinazoline-7-carboxylic acid [3-(2-methyl-piperidine-1-yl)-propyl]-amide (Compound 17) 65 mg (52%) of the target compound was obtained in the same manner of Example 1, using 3-(4-chloro-benzyl)-2,4-dioxoquinazoline-7-carboxylic acid (90 mg, 0.272 mol) obtained in Example 1 and 3-(2-methyl-piperidine-1-yl)-propylamine (103 mL, 0.598 mmol). 1H NMR (400 MHz, DMSO-d6) δ 11.67 (s,1H), 8.72 (bs, 1H), 7.99 (d, J=8.1Hz, 1H), 7.59-7.55 (m, 2H), 7.34 (bs, 4H), 5.05 (s, 2H), 3.26-3.24 (m, 2H), 2.77-2.64 (m, 2H), 2.23 (bs, 2H), 2.04 (bs, 1H), 1.64-1.39 (m, 6H), 1.20 (bs, 2H), 0.96 (bs, 2H).
Reference： [1]Current Patent Assignee: KOREA INSTITUTE OF SCIENCE AND TECHNOLOGY - US2009/54433, 2009, A1
  • 54
  • [ 25560-00-3 ]
  • [ 1062243-48-4 ]
  • [ 1201691-93-1 ]
YieldReaction ConditionsOperation in experiment
Stage #1: 4-(9-cyclopentyl-7,7-difluoro-5-methyl-6-oxo-6,7,8,9-tetrahydro-5H-pyrimido[4,5-b][1,4]diazepin-2-ylamino)-3-methoxy-benzoic acid With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In N,N-dimethyl-formamide for 0.0833333h; Stage #2: 3-(2-Methyl-piperidino)-propylamin In N,N-dimethyl-formamide for 3h; 110 4-(9-cyclopentyl-7,7-difluoro-5-methyl-6-oxo-6,7,8,9-tetrahydro-5H-pyrimido[4,5-b][1,4]diazepin-2-ylamino)-3-methoxy-N-[3-(2-methyl-piperidin-1-yl)-propyl]-benzamide (I-110) A mixture of 0.045 g (0.1 mmole) of 4-(9-cyclopentyl-7,7-difluoro-5-methyl-6-oxo-6,7,8,9-tetrahydro-5H-pyrimido[4,5-b][1,4]diazepin-2-ylamino)-3-methoxybenzoic acid (I-22), 0.042 g (0.110 mmole) of 1-[bis(dimethylamino)methylene]-1H-1,2,3-triazolo[4,5-b]pyridinium-3-oxide hexafluorophosphate, 0.052 ml (0.300 mmole) of ethyldiisopropyl amine and 1.0 mL of dimethylformamide was stirred for 5 minutes and then 0.019 g (0.12 mmole) 3-(2-Methyl-piperidin-1-yl)-propylamine was added. The mixture was stirred for 3 hours, then diluted with 10 mL of water plus 2 mL of saturated aqueous sodium bicarbonate and then extracted 3 times with 10 mL of ethyl acetate. The combined extracts were washed with brine, dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The residue was purified by reverse phase silica gel chromatography, eluding with water-acetonitrile (gradient, 0:100-80:20) to give 0.042 g of 4-(9-cyclopentyl-7,7-difluoro-5-methyl-6-oxo-6,7,8,9-tetrahydro-5H-pyrimido[4,5-b][1,4]diazepin-2-ylamino)-3-methoxy-N-[3-(2-methyl-piperidin-1-yl)-propyl]-benzamide as a white solid.
Reference： [1]Current Patent Assignee: TAKEDA PHARMACEUTICAL COMPANY LIMITED - US2009/318408, 2009, A1 Location in patent: Page/Page column 49
  • 55
  • [ 25560-00-3 ]
  • C44H42FN4O9Pol [ No CAS ]
  • C53H61N6O9Pol [ No CAS ]
YieldReaction ConditionsOperation in experiment
With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide 2 [0111] Synthesis of compounds in soluble form. Small molecule compounds were also synthesized in soluble form for biological tests. In this case, the compounds were synthesized on Rink-amide resin using the scheme shown in Figure 9. In brief, Rink amide MBHA resin (loading 0.59 mmol/g) was first swollen in DMF for 3 h, then Fmoc was removed with 20% piperidine (5 min, 15 min). Alloc-3-amino-3-(4-fluoro-3-nitrophenyl)propanoic acid (scaffold, 3 eq. to resin), HOBt (3 eq.) and DIC (3eq.) were dissolved in DMF and added to the beads. The reaction conducted at room temperature for 4 h. Kaiser test was used to check the completion of the coupling. The beads were washed with DMF, MeOH, DMF. Then, primary amine RiNH2 (5eq.) and DIEA (10eq.) in DMF solution were added to the beads and rotated overnight. NO2 reduction was achieved with 2 M SnCl2*2H2O solution in DMF for 2 h (twice). The beads were washed with DMF, MeOH, DMF again, then R2CHO (5eq.) in DMF was added to the beads and rotated at room temperature for 2 days. After complete washing with DMF, MeOH, DCM, the beads were treated with Pd(PPh3)4 (0.2 eq.) and PhSiH3 (20 eq.) in DCM for 1 h to remove the Alloc group. A DMF solution OfR3NCO (5eq.) in presence of DIEA (lOeq.) was added the beads and rotated for several hours. Kaiser test was used to check the completion of reaction. After the reaction was done, the beads were washed with DMF, MeOH, DCM, then were dried over vacuum. Then, a cleavage solution containing 95% TFA, 2.5% TIS and 2.5% water was added to the beads. After 2 h, the liquid was collected in a 10 mL-tube. After evaporation of TFA and the solvents, the concentrated cleavage product was precipitated with cold ether and purified by semipreparative reversed-phase high-performance liquid chromatography (RP-HPLC). The purity of the ligands was analyzed by analytical RP-HPLC on a Beckman System Gold HPLC system (Fullerton, CA, USA).[0112] The identity of compounds 4,7 and 10 was analyzed on a Thermo Fisher (San Jose, CA) model LCQ equipped with an electrospray source using standard conditions. Compound 4: M/Z 622.4. Compound 7: M/Z 580.35. Compound 10: M/Z 652.35. The structures of remaining compounds were confirmed with a MALDI-TOF MS (see Table 1).
Reference： [1]Current Patent Assignee: UNIVERSITY OF CALIFORNIA - WO2010/39668, 2010, A2 Location in patent: Page/Page column 31-32
  • 56
  • [ 25560-00-3 ]
  • C17H21FN3O7Pol [ No CAS ]
  • C26H40N5O7Pol [ No CAS ]
YieldReaction ConditionsOperation in experiment
With N-ethyl-N,N-diisopropylamine 2 Example 2: Resynthesis of compounds on TG beads and in soluble form[0110] Synthesis on TentaGel beads. By use of the similar synthetic approach described in the library synthesis except an Alloc-protected scaffold (instead of Dde-protected) is used, small molecules No.1-12 (Table 1) were resynthesized on TG beads for re -binding assay. Briefly, TG resin was coupled with the scaffold and split into 12 same portions. And then each same volume of resin was coupled with the corresponding amines using DIEA as a base, followed by NO2 reduction with 2 M SnCl2*2H2O solution in DMF. And then the corresponding aldehydes were coupled to the beads. The Alloc group on the scaffold was deprotected by Pd(PPli3)4/PhSiH3 solution in DCM. These resins were coupled with the corresponding Fmoc-amino acids in presence of HOBt/DIC or isocyanates in presence ofDIEA. For the amino acids at R3 position, Fmoc group was deprotected by 20% piperidine in DMF, and the side chain protecting groups were removed by TFA (94%)/TIS(l%)/H2O (5%).
Reference： [1]Current Patent Assignee: UNIVERSITY OF CALIFORNIA - WO2010/39668, 2010, A2 Location in patent: Page/Page column 31
  • 57
  • [ 25560-00-3 ]
  • [ 1242274-98-1 ]
  • C42H72N6O6 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With titanium(IV) isopropylate In ethanol at 20℃; for 36h;
Reference： [1]Location in patent: experimental part Pettersson, Sofia; Perez-Nueno, Violeta I.; Mena, Maria Pau; Clotet, Bonaventura; Este, Jose A.; Borrell, Jose I.; Teixido, Jordi [ChemMedChem, 2010, vol. 5, # 8, p. 1272 - 1281]
  • 58
  • [ 25560-00-3 ]
  • [ 1316211-08-1 ]
  • [ 75-36-5 ]
  • C52H74N5O3(1+)*Cl(1-) [ No CAS ]
YieldReaction ConditionsOperation in experiment
Stage #1: 3-(2-Methyl-piperidino)-propylamin; Br(1-)*C41H53ClN3O2(1+) With N-ethyl-N,N-diisopropylamine In acetonitrile at 80℃; Stage #2: acetyl chloride With N-ethyl-N,N-diisopropylamine In dichloromethane at 0℃;
Reference： [1]Samanta, Animesh; Maiti, Kaustabh Kumar; Soh, Kiat-Seng; Liao, Xiaojun; Vendrell, Marc; Dinish; Yun, Seong-Wook; Bhuvaneswari, Ramaswamy; Kim, Hyori; Rautela, Shashi; Chung, Junho; Olivo, Malini; Chang, Young-Tae [Angewandte Chemie - International Edition, 2011, vol. 50, # 27, p. 6089 - 6092]
  • 59
  • [ 25560-00-3 ]
  • [ 207399-07-3 ]
  • [ 1501-26-4 ]
  • [ 1313374-54-7 ]
YieldReaction ConditionsOperation in experiment
1 (300 mg, 0.45 mmol, 1 equiv) and l-(3-aminopropyl)-2-pipecoline (170 mg, 0.9 mmol, 2 equiv) were dissolved in ACN (2 mL), and DIEA (87 iL, 0.67 mmol, 1.5 equiv) was added. The reaction mixture was heated at 80 C for 40 minutes, and the resulting blue mixture was neutralized with 0.1 N HCl and concentrated under vacuum. The blue mixture was dissolved in DCM under N2 atmosphere, and treated with excess DIEA (700 iL, 5.39 mmol, 12 equiv) and methyl 4- (chloroformyl)butyrate (110 μ, 0.67 mmol, 1.5 equiv) at 0 C for 15 minutes. The resulting green product 2 was washed with 0.1 N HCl and brine, concentrated under vacuum, and used without further purification.
Reference： [1]Patent: WO2011/119114,2011,A1 .Location in patent: Page/Page column 53
  • 60
  • [ 25560-00-3 ]
  • [ 1375800-66-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: magnesium sulfate / dichloromethane / 96 h / 20 °C / Inert atmosphere 2.1: sodium tetrahydroborate / methanol / 3 h / 0 °C / Inert atmosphere 2.2: 0.17 h / 20 °C 2.3: pH > 10
Reference： [1]Wijtmans, Maikel; Maussang, David; Sirci, Francesco; Scholten, Danny J.; Canals, Meritxell; Mujić-Delić, Azra; Chong, Milagros; Chatalic, Kristell L.S.; Custers, Hans; Janssen, Elwin; De Graaf, Chris; Smit, Martine J.; De Esch, Iwan J.P.; Leurs, Rob [European Journal of Medicinal Chemistry, 2012, vol. 51, p. 184 - 192]
  • 61
  • [ 25560-00-3 ]
  • [ 1375800-44-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: magnesium sulfate / dichloromethane / 96 h / 20 °C / Inert atmosphere 2.1: sodium tetrahydroborate / methanol / 3 h / 0 °C / Inert atmosphere 2.2: 0.17 h / 20 °C 2.3: pH > 10 3.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine / tetrahydrofuran / 1 h / 20 °C / Inert atmosphere 3.2: 0.5 h / 20 °C / Inert atmosphere 3.3: 36 h / 20 °C / Inert atmosphere
Reference： [1]Wijtmans, Maikel; Maussang, David; Sirci, Francesco; Scholten, Danny J.; Canals, Meritxell; Mujić-Delić, Azra; Chong, Milagros; Chatalic, Kristell L.S.; Custers, Hans; Janssen, Elwin; De Graaf, Chris; Smit, Martine J.; De Esch, Iwan J.P.; Leurs, Rob [European Journal of Medicinal Chemistry, 2012, vol. 51, p. 184 - 192]
  • 62
  • [ 25560-00-3 ]
  • [ 15174-47-7 ]
  • C19H28N2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With magnesium sulfate In dichloromethane at 20℃; for 96h; Inert atmosphere; 7.3.3. General procedure B (reductive amination) General procedure: The amine, the aldehyde and MgSO4 (or Na2SO4) were mixed with dry DCM. The mixture was stirred at room temperature for the indicated time (TLC and NMR were used to monitor imine formation). The reaction mixture was filtered and the collected solid was washed with DCM. The filtrate was concentrated in vacuo. MeOH was added to the residue and the mixture was cooled to 0 °C. NaBH4 was added to reduce the imine. The mixture was stirred at 0 °C for the indicated time. The reaction mixture was quenched with acetone, stirred for 10 min at room temperature and concentrated in vacuo. Extraction was performed with H2O/DCM (2x) ensuring that the pH of the water layer is >10 by addition of aq. 10% K2CO3-solution. The combined organic layers were washed with brine (1x), dried over Na2SO4, filtered and concentrated in vacuo. If indicated, the crude product was purified.
Reference： [1]Wijtmans, Maikel; Maussang, David; Sirci, Francesco; Scholten, Danny J.; Canals, Meritxell; Mujić-Delić, Azra; Chong, Milagros; Chatalic, Kristell L.S.; Custers, Hans; Janssen, Elwin; De Graaf, Chris; Smit, Martine J.; De Esch, Iwan J.P.; Leurs, Rob [European Journal of Medicinal Chemistry, 2012, vol. 51, p. 184 - 192]
  • 63
  • [ 25560-00-3 ]
  • S-(2-naphthylmethyl)thioacetimidate hydrobromide [ No CAS ]
  • [ 1417785-59-1 ]
YieldReaction ConditionsOperation in experiment
96% In ethanol at 0 - 20℃;
Reference： [1]MacCallini, Cristina; Ammazzalorso, Alessandra; De Filippis, Barbara; Fantacuzzi, Marialuigia; Giampietro, Letizia; Masella, Simona; Tricca, Maria Luisa; Amoroso, Rosa; Patruno, Antonia; Franceschelli, Sara [Medicinal Chemistry, 2012, vol. 8, # 6, p. 991 - 995,5] MacCallini, Cristina; Patruno, Antonia; Ammazzalorso, Alessandra; De Filippis, Barbara; Fantacuzzi, Marialuigia; Franceschelli, Sara; Giampietro, Letizia; Masella, Simona; Tricca, Maria Luisa; Amoroso, Rosa [Medicinal Chemistry, 2012, vol. 8, # 6, p. 991 - 995]
  • 64
  • [ 25560-00-3 ]
  • [ 623-27-8 ]
  • (S)-N,N'-(1,4-phenylenebis(methylene))bis(3-((S)-2-methylpiperidin-1-yl)propan-1-amine) [ No CAS ]
YieldReaction ConditionsOperation in experiment
With sodium sulfate In methanol for 24h; Reflux; Inert atmosphere;
Reference： [1]Ros-Blanco, Laia; Teixido, Jordi; Borrell, Jose I.; Anido, Judit; Seoane, Joan; Bosser, Ramon; Kosoy, Ana; Ruiz-Avila, Luis; Este, Jose; Clotet, Bonaventura [Journal of Medicinal Chemistry, 2012, vol. 55, # 17, p. 7560 - 7570,11]
  • 65
  • [ 25560-00-3 ]
  • C26H46N4*4ClH [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: sodium sulfate / methanol / 24 h / Reflux; Inert atmosphere 2: sodium tetrahydroborate / methanol / 0 - 20 °C 3: hydrogenchloride / methanol
Reference： [1]Ros-Blanco, Laia; Teixido, Jordi; Borrell, Jose I.; Anido, Judit; Seoane, Joan; Bosser, Ramon; Kosoy, Ana; Ruiz-Avila, Luis; Este, Jose; Clotet, Bonaventura [Journal of Medicinal Chemistry, 2012, vol. 55, # 17, p. 7560 - 7570,11]
  • 66
  • [ 25560-00-3 ]
  • [ 1021920-50-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: sodium sulfate / methanol / 24 h / Reflux; Inert atmosphere 2: sodium tetrahydroborate / methanol / 0 - 20 °C
Reference： [1]Ros-Blanco, Laia; Teixido, Jordi; Borrell, Jose I.; Anido, Judit; Seoane, Joan; Bosser, Ramon; Kosoy, Ana; Ruiz-Avila, Luis; Este, Jose; Clotet, Bonaventura [Journal of Medicinal Chemistry, 2012, vol. 55, # 17, p. 7560 - 7570,11]
  • 67
  • [ 25560-00-3 ]
  • [ 36330-86-6 ]
  • [ 1191119-32-0 ]
YieldReaction ConditionsOperation in experiment
Stage #1: 4-oxo-4-(4-phenoxyphenyl)butanoic acid With diisopropyl-carbodiimide In 1-methyl-pyrrolidin-2-one; 1,2-Dichloropropane for 16h; Automated synthesizer; Stage #2: 3-(2-Methyl-piperidino)-propylamin With triethylamine In 1,2-Dichloropropane for 20h; Automated synthesizer; The TFP resin 4 (0.7 mmol/g, 65 mg, 0.045 mmol) was manually added to each of the 384 wells of an Advanced ChemTech 384 HTS synthesiser. According to the library design each well was treated individually with 37 different carboxylic acids (0.36 mmol) in NMP/DCP (1 :1) (1.5 ml_) followed by DIC (0.028 mL, 0.18 mmol) in NMP (0.1 mL). The array was then shaken for 16 h. The solvents were removed and the acylated resin 5 was washed with NMP (4 x 1 mL) and DCM (10 x 1 mL).According to the library design each well was treated individually with 14 different amines (0.041 mmol) in DCP (1 mL) followed by TEA (8.2 mg, 0.081 mmol) in DCP (0.1 mL). The array was shaken for 20 h and then the reactors were emptied into glass vials. Each reactor well was treated with CH3CN (1 mL) and shaken for 90 min to rinse the resin for product. The washing was emptied into the same set of 4 mL glass vials which were then evaporated to dryness. The residues were dissolved by addition of DMSO (0.25 mL) to each vial. A random subset of 40 samples were analysed by LC-MS showing that the desired compound was present in 83 % of the samples with a purity > 50 %.The average yield of the library was estimated to 50 % and the 384 samples were diluted with DMSO (10 x) and finally with H2O to a final screening concentration of 1.4 μM. The diluted samples were then tested in the automated [35S]GTPyS inhibition assay and the results are shown in Table 1.
Reference： [1]Current Patent Assignee: VTV THERAPEUTICS INC. - WO2009/126782, 2009, A1 Location in patent: Page/Page column 14; 37
  • 68
  • [ 25560-00-3 ]
  • ethyl 2-(dimethylaminomethyleneamino)-4-phenylthiophene-3-carboxylate [ No CAS ]
  • 3-[3-(2-methylpiperidino)propyl]-5-phenylthieno[2,3-d]pyrimidin-4(3H)-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
57% In 5,5-dimethyl-1,3-cyclohexadiene for 30h; Reflux;
Reference： [1]Hovhannisyan, Anna; Aristakesyan, Lilit; Melikyan, Gagik [Heterocyclic Communications, 2012, vol. 18, # 5-6, p. 253 - 256]
  • 69
  • [ 25560-00-3 ]
  • [ 207399-07-3 ]
  • [ 1313374-54-7 ]
YieldReaction ConditionsOperation in experiment
With N-ethyl-N,N-diisopropylamine In acetonitrile at 80℃; for 0.666667h;
Reference： [1]Samanta, Animesh; Vendrell, Marc; Yun, Seong-Wook; Guan, Zhenping; Xu, Qing-Hua; Chang, Young-Tae [Chemistry - An Asian Journal, 2011, vol. 6, # 6, p. 1353 - 1357]
  • 70
  • [ 25560-00-3 ]
  • [ 1313374-55-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: N-ethyl-N,N-diisopropylamine / acetonitrile / 0.67 h / 80 °C 2: hydrogenchloride / tetrahydrofuran; water; chloroform / 12 h / 0 - 80 °C
Reference： [1]Samanta, Animesh; Vendrell, Marc; Yun, Seong-Wook; Guan, Zhenping; Xu, Qing-Hua; Chang, Young-Tae [Chemistry - An Asian Journal, 2011, vol. 6, # 6, p. 1353 - 1357]
  • 71
  • [ 25560-00-3 ]
  • [ 1313513-58-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: N-ethyl-N,N-diisopropylamine / acetonitrile / 0.67 h / 80 °C 2.1: hydrogenchloride / tetrahydrofuran; water; chloroform / 12 h / 0 - 80 °C 3.1: dicyclohexyl-carbodiimide / tetrahydrofuran / 0.17 h / 20 °C 3.2: 12 h / 20 °C
Reference： [1]Samanta, Animesh; Vendrell, Marc; Yun, Seong-Wook; Guan, Zhenping; Xu, Qing-Hua; Chang, Young-Tae [Chemistry - An Asian Journal, 2011, vol. 6, # 6, p. 1353 - 1357]
  • 72
  • [ 25560-00-3 ]
  • [ 1603109-83-6 ]
  • C31H45N3O6 [ No CAS ]
YieldReaction ConditionsOperation in experiment
96% In toluene Reflux;
Reference： [1]Jeong, Yong-Chul; Anwar, Muhammad; Moloney, Mark G. [Bioorganic and Medicinal Chemistry Letters, 2014, vol. 24, # 8, p. 1901 - 1906]
  • 73
  • [ 25560-00-3 ]
  • 3-(2-((1r,3r)-adamantan-1-yl)-1-hydroxyethylidene)-1-butyrylpyrrolidine-2,4-dione [ No CAS ]
  • C29H45N3O3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
72% In toluene Reflux;
Reference： [1]Jeong, Yong-Chul; Anwar, Muhammad; Moloney, Mark G. [Bioorganic and Medicinal Chemistry Letters, 2014, vol. 24, # 8, p. 1901 - 1906]
  • 74
  • [ 25560-00-3 ]
  • C22H20BrClNPol [ No CAS ]
  • C31H39ClN3Pol [ No CAS ]
YieldReaction ConditionsOperation in experiment
With N-ethyl-N,N-diisopropylamine In 1-methyl-pyrrolidin-2-one at 70℃; for 12h;
Reference： [1]Agrawalla, Bikram Keshari; Chandran, Yogeswari; Phue, Wut-Hmone; Lee, Sung-Chan; Jeong, Yun-Mi; Wan, Si Yan Diana; Kang, Nam-Young; Chang, Young-Tae [Journal of the American Chemical Society, 2015, vol. 137, # 16, p. 5355 - 5362]
  • 75
  • [ 25560-00-3 ]
  • C20H28N2O4 [ No CAS ]
  • C29H46N4O3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Reflux; 3.6. Synthesis of 3-Carboxamide an 3-Enamine Barbituric Acids General procedure: General procedure: To the solution of 3-alkoxycarbonyl or 3-acylbarbituric acid (1.0 equivalent) in toluene (or methanol for compound 36) was added primary amine (1.0 equivalent) and the mixture was refluxed for 4-24 h checking TLC. After completion of the reaction, the solution was evaporated and column chromatography (or precipitation in methanol for compound 36) gave metal-chelated 3-carboxamide tetramic acid or pure 3-enamine tetramic acid. In case of 3-carboxamide tetramic acid, the compound was dissolved in dichloromethane (50 mL) and washed with 1 N HCl (20 mL) to make metal free form. The organic layer was dried with MgSO4 and concentrated in vacuo to give metal free 3-carboxamide tetramic acid.
Reference： [1]Jeong, Yong-Chul; Moloney, Mark G. [Molecules, 2015, vol. 20, # 3, p. 3582 - 3627]
  • 76
  • [ 25560-00-3 ]
  • methyl 4-chloro-2-(3-methoxybenzyl)-9H-pyrido[2’,3’:4,5]pyrrolo[2,3-d]pyrimidine-7-carboxylate [ No CAS ]
  • methyl 2-(3-methoxybenzyl)-4-((3-(2-methylpiperidin-1-yl)propyl)amino)-9H-pyrido[2’,3’:4,5]pyrrolo[2,3-d]pyrimidine-7-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
0.024 g With triethylamine In methanol at 140℃; for 0.75h; Microwave irradiation; 4 Intermediate 40 A mixture of intermediate 4B (0.060 g, 0.15 mmol), 3-(2-methylpiperidin-1-yl)propan-1 -amine (0.073 g, 0.47mmol) and Et3N (0.044 ml, 0.31 mmol) in methanol (0.7 ml) was heated at 140°C for 45 mm in a microwaveapparatus. The solvent was removed under vacuum and the residue purified on ISCO with a RediSepcolumn using DCM-MeOH-NH4OH (80-20-2.5%) to furnish 0.024 g of the title compound. 1H NMR (400MHz, DMS0-d6) ö ppm 0.97 (d, J=6.3 Hz, 3 H) 1.23- 1.36 (m, 2 H) 1.49- 1.64 (m, 4 H) 1.70- 1.85 (m, 2H) 1.95-2.08 (m, 1 H) 2.16-2.31 (m, 2 H) 2.70-2.91 (m, 2 H) 3.65-3.71 (m, 2 H) 3.72 (5, 3 H) 3.91 (5, 3H) 4.03 (5, 2 H) 6.77 (dd, J=8.2, 1.9 Hz, 1 H) 6.92 - 6.99 (m, 2 H) 7.19 (t, J=7.8 Hz, 1 H) 7.6 (t, J=5.6 Hz, 1H) 8.18 (d, J=1.6 Hz, 1 H) 8.96 (d, J=1.6 Hz, 1 H) 12.21 (br. s., 1 H). HRMS m/z 503.2771 (M+H)t
Reference： [1]Current Patent Assignee: UNIVERSITY OF MONTREAL - WO2015/161373, 2015, A1 Location in patent: Page/Page column 52; 53
  • 77
  • [ 25560-00-3 ]
  • 2-(4-(bromomethyl)phenyl)-N-(3-morpholinopropyl)acetamide [ No CAS ]
  • 2-(4-((3-(2-methylpiperidin-1-yl)propylamino)methyl)phenyl)-N-(3-morpholinopropyl)acetamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
20% With potassium carbonate In methanol; acetonitrile at 0 - 150℃; for 0.416667h; Microwave irradiation;
Reference： [1]Puig De La Bellacasa, Raimon; Gibert, Albert; Planesas, Jesús M.; Ros-Blanco, Laia; Batllori, Xavier; Badía, Roger; Clotet, Bonaventura; Esté, José; Teixidó, Jordi; Borrell, José I. [Organic and Biomolecular Chemistry, 2016, vol. 14, # 4, p. 1455 - 1472]
  • 78
  • [ 25560-00-3 ]
  • 2-(4-(bromomethyl)phenyl)-N-(3-(piperidin-1-yl)propyl)acetamide [ No CAS ]
  • 2-(4-((3-(2-methylpiperidin-1-yl)propylamino)methyl)phenyl)-N-(3-(piperidin-1-yl)propyl)acetamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
27% With potassium carbonate In methanol; acetonitrile at 0 - 150℃; for 0.416667h; Microwave irradiation;
Reference： [1]Puig De La Bellacasa, Raimon; Gibert, Albert; Planesas, Jesús M.; Ros-Blanco, Laia; Batllori, Xavier; Badía, Roger; Clotet, Bonaventura; Esté, José; Teixidó, Jordi; Borrell, José I. [Organic and Biomolecular Chemistry, 2016, vol. 14, # 4, p. 1455 - 1472]
  • 79
  • [ 25560-00-3 ]
  • 2-(4-(bromomethyl)phenyl)-N-(3-(2-methylpiperidin-1-yl)propyl)acetamide [ No CAS ]
  • 2-(4-((3-(2-methylpiperidin-1-yl)propylamino)methyl)phenyl)-N-(3-(2-methylpiperidin-1-yl)propyl)acetamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
32% With potassium carbonate In methanol; acetonitrile at 0 - 150℃; for 0.416667h; Microwave irradiation;
Reference： [1]Puig De La Bellacasa, Raimon; Gibert, Albert; Planesas, Jesús M.; Ros-Blanco, Laia; Batllori, Xavier; Badía, Roger; Clotet, Bonaventura; Esté, José; Teixidó, Jordi; Borrell, José I. [Organic and Biomolecular Chemistry, 2016, vol. 14, # 4, p. 1455 - 1472]
  • 80
  • [ 25560-00-3 ]
  • [ 21062-19-1 ]
  • [ 1351472-55-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: triethylamine / dichloromethane / 0 - 20 °C / Inert atmosphere 2.1: dimethylsulfide borane complex / tetrahydrofuran / 6 h / Inert atmosphere; Reflux 2.2: 1 h / Reflux
Reference： [1]Puig De La Bellacasa, Raimon; Gibert, Albert; Planesas, Jesús M.; Ros-Blanco, Laia; Batllori, Xavier; Badía, Roger; Clotet, Bonaventura; Esté, José; Teixidó, Jordi; Borrell, José I. [Organic and Biomolecular Chemistry, 2016, vol. 14, # 4, p. 1455 - 1472]
  • 81
  • [ 25560-00-3 ]
  • [ 21062-19-1 ]
  • N,N′-bis(3-(2-pipecolin-1-yl)propyl)-1,4-di(aminocarbonylmethyl)benzene [ No CAS ]
YieldReaction ConditionsOperation in experiment
71% With triethylamine In dichloromethane at 0 - 20℃; Inert atmosphere;
Reference： [1]Puig De La Bellacasa, Raimon; Gibert, Albert; Planesas, Jesús M.; Ros-Blanco, Laia; Batllori, Xavier; Badía, Roger; Clotet, Bonaventura; Esté, José; Teixidó, Jordi; Borrell, José I. [Organic and Biomolecular Chemistry, 2016, vol. 14, # 4, p. 1455 - 1472]
  • 82
  • [ 25560-00-3 ]
  • [ 119549-47-2 ]
  • 2-(4-(bromomethyl)phenyl)-N-(3-(2-methylpiperidin-1-yl)propyl)acetamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
20% With potassium carbonate In acetonitrile at 100℃; for 0.416667h; Microwave irradiation;
Reference： [1]Puig De La Bellacasa, Raimon; Gibert, Albert; Planesas, Jesús M.; Ros-Blanco, Laia; Batllori, Xavier; Badía, Roger; Clotet, Bonaventura; Esté, José; Teixidó, Jordi; Borrell, José I. [Organic and Biomolecular Chemistry, 2016, vol. 14, # 4, p. 1455 - 1472]
  • 83
  • [ 25560-00-3 ]
  • C62H87N6O10S2(1+) [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: N-ethyl-N,N-diisopropylamine / acetonitrile / 2.5 h / 0 - 20 °C 2: N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / dimethyl sulfoxide; N,N-dimethyl-formamide / 3 h / 20 °C 3: trifluoroacetic acid / dichloromethane / 3 h / 20 °C
Reference： [1]Su, Dongdong; Teoh, Chai Lean; Park, Sung-Jin; Kim, Jong-Jin; Samanta, Animesh; Bi, Renzhe; Dinish; Olivo, Malini; Piantino, Marie; Louis, Fiona; Matsusaki, Michiya; Kim, Seong Soon; Bae, Myung Ae; Chang, Young-Tae [Chem, 2018, vol. 4, # 5, p. 1128 - 1138]
  • 84
  • [ 25560-00-3 ]
  • [ 5292-43-3 ]
  • C15H30N2O2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With N-ethyl-N,N-diisopropylamine In acetonitrile at 0 - 20℃; for 2.5h; General procedure: The BOC protected diversity building blocks were prepared from tert-butyl 2-bromoacetate towhich was added the different primary amine. To a stirred solution of the primary amine and 1equiv. of DIEA in 3 mL acetonitrile, 1 equiv. of tert-butyl 2-bromoacetate was added slowly in 0oC.After stirring in 0oC for 30 min, the reaction mixture was warmed to rt and stirred for 2 hr. Aftercompletion of the reaction, the solvent was concentrated in vacuum. The residue was purified bycolumn chromatography on silica gel (DCM: MeOH =95:5) to afford the amine linker as lightyellow oil. 64 different aromatic and aliphatic primary amines were used for diversity buildingblocks synthesis and the yields are between 40 %-60 %.
Reference： [1]Su, Dongdong; Teoh, Chai Lean; Park, Sung-Jin; Kim, Jong-Jin; Samanta, Animesh; Bi, Renzhe; Dinish; Olivo, Malini; Piantino, Marie; Louis, Fiona; Matsusaki, Michiya; Kim, Seong Soon; Bae, Myung Ae; Chang, Young-Tae [Chem, 2018, vol. 4, # 5, p. 1128 - 1138]
  • 85
  • [ 25560-00-3 ]
  • [ 5292-43-3 ]
  • C66H95N6O10S2(1+) [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: N-ethyl-N,N-diisopropylamine / acetonitrile / 2.5 h / 0 - 20 °C 2: N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / dimethyl sulfoxide; N,N-dimethyl-formamide / 3 h / 20 °C
Reference： [1]Su, Dongdong; Teoh, Chai Lean; Park, Sung-Jin; Kim, Jong-Jin; Samanta, Animesh; Bi, Renzhe; Dinish; Olivo, Malini; Piantino, Marie; Louis, Fiona; Matsusaki, Michiya; Kim, Seong Soon; Bae, Myung Ae; Chang, Young-Tae [Chem, 2018, vol. 4, # 5, p. 1128 - 1138]
  • 86
  • [ 25560-00-3 ]
  • [ 117-80-6 ]
  • 2-(3-(2-methylpiperidin-1-yl)propylamino)-3-chloronaphthalene-1,4-dione [ No CAS ]
YieldReaction ConditionsOperation in experiment
40% In ethanol at 20℃;
Reference： [1]Kacmaz, Aysecik; Deniz, Nahide Gulsah; Aydinli, Serdar Goksin; Sayil, Cigdem; Onay-Ucar, Evren; Mertoglu, Elif; Arda, Nazli [Open Chemistry, 2019, vol. 17, # 1, p. 337 - 345]
  • 87
  • [ 25560-00-3 ]
  • [ 137234-74-3 ]
  • C15H25FN4 [ No CAS ]
  • C15H25ClN4 [ No CAS ]
Reference： [1]ACS Combinatorial Science,2020
  • 88
  • [ 25560-00-3 ]
  • [ 1821-12-1 ]
  • N‑(3‑(2‑methylpiperidin‑1‑yl)propyl)‑4‑phenylbutanamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
75% With O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; triethylamine In ethyl acetate at 20℃; for 12h; General procedure for the synthesisof amides (2-5) or esters (1, 6)in the presence of 2-(1H-Benzotriazole-1-yl)-1,1,3,3-tetramethylaminium tetrafluoroborate(TBTU) General procedure: The compounds were synthesized by following the describedprotocol [42]. Briefly, 4-phenylbutyric acid (4-PBA)(1 mmol, 1 eq, 164.2 mg) was dissolved in ethyl acetate(EtOAc) (30 ml) and TBTU (1 mmol, 1 eq, 321 mg) andtriethylamine (TEA) (2 mmol, 2 eq, 0.27 ml) were added.The mixture was stirred until a clear solution was achieved;then the appropriate amine (2 mmol, 2 eq) was added. Afterhaving been stirred for 12 h at room temperature, the mixture was washed with H2O(3 × 50 ml) and the organic phasewas separated, dried over anhydrous Na2SO4,filtered, andevaporated at reduced pressure to obtain a crude product.Appropriate purification of the crude mixture afforded correspondingcompounds 1-6. The compounds were also characterizedby HRMS and NMR.
Reference： [1]Azoulay-Ginsburg, Salome; Di Salvio, Michela; Weitman, Michal; Afri, Michal; Ribeiro, Sara; Ebbinghaus, Simon; Cestra, Gianluca; Gruzman, Arie [Pharmacological Reports, 2021, vol. 73, # 2, p. 536 - 550]
  • 89
  • [ 25560-00-3 ]
  • C37H49FO3 [ No CAS ]
  • C46H67FN2O2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Stage #1: C37H49FO3 With benzotriazol-1-ol; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 0.5h; Stage #2: 3-(2-Methyl-piperidino)-propylamin In dichloromethane at 20℃; for 12h;
Reference： [1]Gu, Wen; Li, A-Liang; Liu, Qing-Song; Sun, Yue; Wang, Wen-Yan; Yang, Zi-Hui [New Journal of Chemistry, 2022, vol. 46, # 5, p. 2335 - 2350]

Tags: 25560-00-3 synthesis path| 25560-00-3 SDS| 25560-00-3 COA| 25560-00-3 purity| 25560-00-3 application| 25560-00-3 NMR| 25560-00-3 COA| 25560-00-3 structure

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Chemistry
Heterocyclic Building Blocks
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Chemistry
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Piperidines
methylpiperidine
Chemistry
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Aliphatic Heterocycles
Chemistry
Organic Building Blocks
Amines
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